Humorous Moments in Crossdressing 2

Hot Tipic skirt

I offer you another humorous moment in the crossdressing life of yours truly. This was probably more embarrassing than humorous, at least for me. Life is full of moments like this. It’s just a lot more interesting when crossdressing is involved… or maybe just that much more humorous. I’m cool with it though. I hope this humorous (and embarrassing) moment in my life offers you a good laugh or two.

My wife and I were out shopping at a local mall. I was in guy-mode – just another plain looking guy, not much to look at. While browsing a store called “Hot Topic”, my wife spotted a pretty cool skirt. With much excitement she turned toward me, held the skirt up to me, and blurted out in a not so subtle voice, “Honey, you’d look so good in this skirt!” That might have been rather embarrassing if we were out in a public place filled with people and I was in guy-mode. Wait a minute… we were out in a public place filled with people and I was in guy-mode! :o

When we’re out shopping for my female clothing, there are certain protocols to follow. We both refer to Gabrielle as if she’s a friend of my wife’s. She was supposed to say “Don’t you think Gabrielle would look good in this?”, however that is not how it came out at all.

So there I was, out in public in guy-mode. My wife was holding a skirt up to me after letting everyone in a 20 foot radius know how good I’d look in it. I’m not sure exactly what shade of red I turned, but there was nothing I could do other than laugh. As soon as she realized what she just did, Mrs. H. began laughing as well. Embarrassing or not, it was rather funny. Even though I’m sure that people in close proximity heard exactly what she said, it’s the kind of store where the employees and regular customers tend to be a little more open-minded and don’t frown upon personal differences so much. No real damage done.

They didn’t have the skirt in my size, but we picked up a cool black mesh top and some fishnet stockings. I do love my fishnets. I wish they weren’t considered part of a “cheap” or “slutty” look by so many people, but that is an entirely different hot topic for another day.

As much as I hate how society treats crossdressers and transgendered people, you have to admit – it does make for some rather humorous moments at times. :)

Related content: More Humorous Moments in Crossdressing


16 thoughts on “Humorous Moments in Crossdressing 2”

  1. Gabrielle may I suggest a custom made kilt from I have 2 in the semi-traditional style. They wear well and are machine washable. Excellent price for a custom made kilt. If you like you can wear the pleats to the front. Traditionally they are worn to the rear. Good luck… Kilts normally worn by boys or men Kilted skirts worn by women…. Remember what Ricky Nelson said… You can’t please everyone so you might as well please yourself.

    1. I appreciate the suggestion, Nancy. :) I think I’ll stick to skirts though. I love skirts and I’m a bit too girly for a kilt (even though there is sometimes little difference visually). Besides, if I were kilt shopping and Mrs. H. did what she did, there’d really be no humor in it, right? lol

  2. Gabrielle, I luv your site, hon! Embarrassing moments are just one of the thrills that come with wearing frills, dearie!

    1. Thanks, Gina. :) Life is full of unexpected awkward moments. May as well just enjoy them, right? lol At the very least, they make for fun stories to share.

  3. Hey Gab’s.. just followed your link here.. just wanted to say how cool i think you are… just read the above and i swear to god the exact! same thing happened to me yesterday.. i hate getting embarrassed by things like that.. spose i just got caught of guard…. Still pretty funny! & the skirt didn’t fit me either!..


  4. Hi Gabrielle I agree but a have a humorous story. One time while shopping for underwear at a large outlet in Pa. The clerk asked if they were for me. I was in man mode. So I said I don’t know for sure until I get home and try them on. I love verbal ping-pong. Hope you have a nice weekend. Will be watching the Indy 500 this weekend. Hope everyone on the website has a great time with their families.

  5. hey,,,sooo funny,,,was that hot topics in the maine mall? sooo cool,,, I love that shop

  6. Yea, Hot Topic is probably one of the stores that would be more tolerant of this type of occurence.

    My wife and I try to use the same “code” while out shopping, e.g. “I’m going to buy this for Jessica”.

  7. firstly, rock on! i also shop at hot topic! i love it!

    secondly, yes that is pretty funny. one of my ex girlfriends did almost the exact same thing when we were at hotopic one day. she found a really cute corset style top that was black with red lace, and held it up to me and said “you would be so hot in this!”(note the exclamation point.) needless to say everyone heard her. but i didnt care. she says stuff like that all the time. shes pretty “weird” herself, so one took any real notice.

    hot topic is a great place to shop for people like us. the clerks and costumers are really openminded. they pretty much have to be. thats what hottopic all about really.

    1. Yeah, I like Hot Topic a lot, Brittany. It sounds like it’s the increasingly popular place to be accidentally outed by our significant other. lol

      I do like the open-minded atmosphere there. The sales assistants are cool, friendly, and fun to chat with. Sooner or later, I’ll probably end up stopping in the store wearing what I bought there. :)

  8. haha, that’s funny, my wife has done the same thing on more than one occassion. Though we are very private about it in general, I try to just roll with it. having a supportive and enthusiastic wife, albeit with an inability to stick to the protocol, is very cool. I’m thankful. great site! – Ash

    1. Thanks, Ashley. :) Yeah, embarrassing moments do happen from time to time. They’re usually more funny than embarrassing, though. I’ve got a pretty good sense of humor about myself and my life. Got to enjoy the humorous moments in life whenever you can, right? Glad your wife is supportive as well. Send her my love, and y’all have a beautiful day! :)

  9. Hot topic is a Goth based store line. Thus, they are open minded. No one batted an eye when I was asking if they had a black tiered skirt that I needed for a costume I was working….while I was wearing a long black skirt, T shirt, and reversed driving cap, covered over by a trench coat. I fit Goth, and was quite obviously in male androgynous mode. LOL. The one Hot Topic in my area it is not unusual for the male clerks to be in all black outfits that consist of mini skirts, black tights, BIG boots, chains, fancy shirt, accessories and so on. I love it when I see it, and always give compliments. But I also compliment the girls when they also wear something wild. Lately though black jeans have dominated my hot topic, which is irritating.

  10. Hi,
    Loved your story. I have one, too. My girlfriend and I were celebrationg our first Halloween together. She knew about Kay and suggested we go as Mae West and W.C. Fields. We had a great time shopping for a gown for my Mae debut. Shopping in guy mode, we picked out two gowns that we thought would work and bought both of them. A white dress with long angel like sleves and a green low cut with fringe. My girlfriend was anxious to see me in them and said lets go to one of her girl friend’s house that lived close by. We explained our plan for the party and her girlfriend said lets see the gowns.Go try them on.I pretended to protest as she had a daughter that was 3 or 4 working on a coloring books on the floor. I asked wouldn’t see be tramatized to see a guy in a dress? They said don’t be silly. We want a fashion show. Reluctantly, (wink) I took the gowns a went in to change. I modeled one and then the other. Both fit great. They made their comments and the little girl seemed unfazed. She just continued coloring and I never saw her look up. Finally, both gals agreed on the white dress. Her friend made us promise to stop by before the party so she could see the final results.

    On that night, with blond hair, make-up, a big hat, a boa, high heels and fish nets, I figured the little girl would not recognize me or remember that day weeks earlier. Unfortunately, I was wrong. She took one look at me and said, ” I liked you better in the green,” As she got older and her mom reminded her of the story she would repeat that line every time she saw me.


Comments are closed.